


Thoughtless

by ProfoundlyInLove



Series: Oops killed another one [5]
Category: Supernatural
Genre: Break Up, F/M, Hurt Dean Winchester, Long-Distance Relationship, Long-Term Relationship(s)
Language: English
Status: Completed
Published: 2014-08-01
Updated: 2014-08-01
Packaged: 2018-02-11 08:59:43
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,191
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2062032
Author URL: https://archiveofourown.org/users/ProfoundlyInLove/pseuds/ProfoundlyInLove
Summary: <blockquote class="userstuff">
              <p>He loved her first.</p>
            </blockquote>





	Thoughtless

**Author's Note:**

> New ship that I've fallen in love with.

When Dean was nineteen, he was recovering from a wendigo related injury in a podunk in the middle of Iowa. He’d broken a rib and had some pretty hefty bruising though some of it was unrelated… So he was left alone while Sam was out researching for Dad while Dad was doing surveillance for the next forty eight hours.

Somewhere during that time, Dean ran out of food and had no choice but to leave the room to find a store. Despite the insane amount of pain, he was able to maneuver his body into the Impala. The closest store was the Walgreens around the corner where he’d gotten his pain medication after the hospital visit. That had been difficult, his father was yelling at everyone and Sam was terrified, while Dean was barely conscious and in a lot of pain.

So when he walked into the Walgreens the first time, he didn’t even really see the gorgeous blonde haired blue eyed beauty at the register. But today, he sure did. When he finally gathered all of his items, he placed them on her counter carefully. ‘Jess’ her name tag said. She smiled at him, it was like pure sunshine in this cloudy and dreary town.

“Hey, I’m Dean.” He said, smiling brightly at her. Dean would never admit he wa blushing, but he totally was.

“Well Dean, you look like you took a hell of a beating,”She frowned, reaching across the counter to cup his cheek with one hand, right under his black eye. She brushed her thumb across his skin before pulling back, blushing.

“Sorry, that was really inappropriate, I’ll just ring you up and..”

“I never said I didn’t like it,” He chuckled as she gave him his receipt. He grasped the pen chained to the counter and flipper over the receipt to the blank side. In scratchy small hand writing he wrote down his phone number and email address.

“Say hi sometime, I’d really like it.” He smiled as he pushed the receipt back to her before gathering his bag of food, leaving with a bright smile on his face.

They emailed, texted and called for the next three and a half years. She knew all his secrets, and he knew hers. the hunting, daddy issues, abuse, everything. He’d learned that she’d been seventeen, now twenty. She lived with foster parents, hated rap music and loved to dance. Whenever he was in the area, he’d spend his time with Jess, no matter the repercussions. Over time, they’d fallen in love. The kind of love where you can’t take your eyes off them, every touch is electric, and every day with them is the new best day of your life.

But after Sam left for Stanford, their lives were disrupted. Dean had to keep his drunk father afloat, leaving him no time for anything. He never had a moment to himself, let alone with Jess. Dean did the most heartbreaking thing he’d ever done-- He broke up with Jess. Not because they were no longer in love or they had problems. Dean believed that he couldn’t be what Jess deserved, she was a Stanford attending, genius, beautiful woman that Dean never deserved.

_Jess, You deserve better than me.. I still love you and I always will. But I’ve got to let you go. I hope I see you again one day, but for now this is goodbye. Love, Dean._

Dean threw himself into the cases after that, refusing to acknowledge he’d let go the best thing that ever happened to him. But things got complicated when Dad disappeared on a hunting trip. That how he found himself wondering around in the dark in his estranged brothers home.

“What the hell are you doing here, Dean?” Sam asked after pinning his older brother to the floor.

“I was lookin’ for a beer.” Dean smiled, attempting to break the tension.

“What are you doing here, Dean.” Sam said again, growing frustrated.

“Okay, alright, we gotta talk.” Dean frowned. His dorky brother had changed into a grown man the size of a moose.

“Uh.. A phone?” Sam said, outwardly frustrated.

“If I’d’a called, would you have picked up?”

The light flicked on, illuminating the room. “Sam?” She’d said, causing them both to snap their heads in that direction. Dean’s heart to stop and try to jump out of his chest. She was in underwear and a smurf tshirt the had a cut out vneck.

“Dean, this is my girlfriend Jessica.” Sam said coolly, as if nothing were wrong at all. Simply because he just didn’t know. He’d always been a little unobservant.

“Wait, your brother Dean?” She said, her voice shook as she looked Dean up and down. He was different from the last she saw him. Taller, voice was deeper, hair was a little longer, and a stronger build.

“I love the smurfs,” He said with faux goofiness. Jess used to watch the smurfs in the morning when they’d be eating cereal while curled up on the couch. They were far from hunting and possible death, everything felt right. Those were the best times of his life, and everything he sacrificed for the time he spent with her was worth it.

“Now I gotta tell you, you are completely out of my brothers league.” He said coming closer to Jess who was so nervous she could crumble. But Dean’s smile kept her standing, even though it was like seeing the sun for the first time.

“Just.. Let me put something on.” She said flatly, all she wanted to do was reach out and touch him, but she couldn’t and that killed her inside.

“No, no, I wouldn’t dream of it...seriously.” He said, at a loss for words. She looked at him disappointedly as he backed away.

“Hey, I gotta borrow your _boyfriend_ here, we gotta talk about some private family business.” He said with heavy emphasis on boyfriend. “Nice meetin’ you.” That wasn’t a lie, the first day he met her had been one of the nicest nights of his life.

“No, no, whatever you gotta say, you can say it infront of her.” Sam said, stepping to Jess’ side.

“Okay, um, Dad hasn’t been home in a few days.” He said flatly, trying to avoid looking at her because he may just melt.

“So?...” Sam said, he carried on but Dean didn’t particularly care for what he had to say.

“Dad’s on a hunting trip, and hasn’t been home in a few days.” He said, emphasis on hunting.

“Jess excuse us.”

As Sam was loading a bag into the car, Dean caught a moment with Jess alone.

“My brother? _Really_? Out of all the people out there, you choose him. I can’t believe you.” Dean said in a rushed quiet voice, filled with hurt.

“I saw you in him.That’s all I really wanted.”

  
Six months after she died in a fire while they set out to find their Dad, when Sam says ‘Jess died six months ago, you don’t know shit about what I feel!’ He keeps quiet, because he does, because he loved her too.


End file.
